Reaktion #1811099

Reaktionsgleichung

aldehyde

1-(4-Fluoro-phenyl)4a-methyl-4,4a,5,6,7,8-hexahydro-1H-benzo[f]indazole-5-carbaldehyde

anthracene-9-carboxaldehyde

THF

→

( 269 )

Ausbeute 78.0%

6-Anthracen-9-ylmethylene-1-(4-fluoro-phenyl)4a-methyl-1,4,4a,6,7,8-hexahydro-benzo[f]indazol-5-one

Ausbeute 78.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction was quenched with 5 mL of saturated aqueous ammonium chloride
2. 2
   ExtraktionThe aqueous layer was extracted with ether (3×10 mL)
3. 3
   Waschenthe pooled organic extracts were washed with brine (10 mL)
4. 4
   Trocknendried (MgSO4)
5. 5
   Einengenconcentrated

Vorschrift

In a 100 mL round bottom flask, aldehyde (207) (100 mg, 0.337 mmol) and anthracene-9-carboxaldehyde (349 mg, 1.69 mmol) were dissolved in 10 mL THF and cooled to 0° C. Lithium hexamethyldisilylamide (LHMDS) (370 μL, 0.370 mmol) was added dropwise, and the solution was stirred at room temperature for 16 hours. The reaction was quenched with 5 mL of saturated aqueous ammonium chloride. The aqueous layer was extracted with ether (3×10 mL), and the pooled organic extracts were washed with brine (10 mL), dried (MgSO4) and then concentrated. Flash chromatography of the residue (0-25% EtOAc/hexanes) gave (269) (127.9mg, 78%).

Quelle